Gary Vee winning mindset, builder of businesses and people, masterclass of evolution, overcoming self-doubt, key to adaptability, 3 life tips to implement, reveals next big trend and explains underlying issue of parental connection to grown kids.

Pivot Podcast

The Pivot Podcast Network

Sports, Football, Society & Culture

4.9 • 3.1K Ratings

🗓️ 10 February 2026

⏱️ 58 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

“There's something sort of romantic about losing everything and going back to zero.” Garry Vee Continuing to champion a winning mindset after Super Bowl week, We sit down with serial entrepreneur, investor, cultural icon and friend of The Pivot Gary Vaynerchuk, better known to the world as Gary Vee. From immigrating to the U.S. as a kid and transforming his family’s liquor store into a multimillion-dollar business, to building VaynerMedia and becoming one of the most influential voices in entrepreneurship, Gary’s journey is all about betting on yourself and embracing the long game. Gary dives right in on the do's and don'ts of navigating everyday life, offering research and guidance whether you are someone who feels stuck, looking for the next thing or experiencing self-doubt, he shares something for everyone in this conversation by making complex ideas seem relatable and breaking down what's hold someone back. He breaks down the fears associated with AI and how, electricity, something we couldn't live without now, was once feared that same way. Gary gets real about taking chances before you’re ready, the fears that still drive him, and why self-awareness is the ultimate competitive advantage. He breaks down what most people get wrong about success, money, and happiness, and why patience, humility, and execution matter more than hype. The conversation also dives into emerging business and media trends, where attention is really going in 2026, and how creators, athletes, and entrepreneurs can stay ahead without burning out. Plus, Gary connects his passion for sports to leadership, ownership, and legacy—and explains why athletes are perfectly positioned to dominate the business world if they play it right. This is a masterclass in mindset, risk, and evolution from someone who’s lived every chapter and has a willingness to share information hoping to make an impact. Pivot Family, please like, comment and hit the subscribe button, we love hearing from you! Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0	Ready to launch your business? Get started with the commerce platform made for entrepreneurs.
0:04.6	Shopify is specially designed to help you start, run and grow your business with easy, customizable themes that let you build your brand, marketing tools that get your products out there.
0:14.1	Integrated shipping solutions that actually save you time. From startups to scaleups, online, in person and on the go.
0:21.0	Shopify is made for entrepreneurs like you.
0:23.4	Sign up for your $1 a month trial at Shopify.com slash setup.
0:28.5	If you had all the money you could ever want, would you be willing to lose it all?
0:33.5	For many people, that answer is no, but for today's guest, Gary Vaynerchuk, he's more than
0:39.0	willing to lose it all.
0:40.5	Gary V, as he's known to many, grew up working in his pop's liquor store.
0:44.6	It was right in the middle of the tracks.
0:46.6	Half of the patrons came in and they bought $6.40 ounces, and the other half bought $1,000
0:53.1	bottles of wine. He's the man who runs Vayner Sports, V.1,000 bottles of wine.
0:59.8	He's the man who runs Vayner Sports v. Friends and Vayner Media along with a host of other businesses. And he's not done spreading the knowledge of how they've grown. In fact, he's just
1:05.8	getting started. I mean, dude walked in with so much energy and never once did he skip a beat.
1:12.3	He dropped gym after gym after gym on business, life, and the principles of true earners.
1:19.3	Gary Vee is fearless when it comes to business and honestly, that's his number one superpower.
1:25.2	He's not scared to go big or lose big, as long as his family will be
1:30.0	straight. Somehow, he's built this massive public brand while keeping his private life private.
1:36.7	That is, until today, he'll open the doors to the House of Vayner just a little bit.
1:42.4	So sit back and relax as Gary Vee takes us to school, which ironically is the only room he
1:49.5	didn't excel in.
1:50.7	So it's the pivot with me, Chan, Freddie T and Gary V.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from The Pivot Podcast Network, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of The Pivot Podcast Network and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.